Organic Chemistry for Engineers

School of Chemical and Biomedical Engineering

Electrophilic aromatic substitution

Question 1
a. Aniline reacts with nitrous acid, , to yield a stable diazonium salt. This
diazonium salt undergoes electrophilic aromatic substitution on activated aromatic
rings to yield brightly colored azo compounds that are widely used as dyes. The
intermediate structures for the mechanism of this reaction are given below. Show
all electron flow with arrows for this mechanism on the structures provided.

Answer1 (a):
Question 2

ANS 2 a:

ANS 2b:

ANS c:

ANS d:

ANS e:
Question 3
Propose syntheses to carry out each of the following conversions starting from
benzene.

a. b. c.

Ans 3a:

Ans 3b.

Ans 3c.